{4,6-Dichloro-2-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-­yl)imino­meth­yl]phenolato-κ²N,O}copper(II)

In the mononuclear title complex, [Cu(C₁₈H₁₄Cl₂N₃O₂)₂], the Cu^II atom is coordinated by two N atoms and two O atoms from the Schiff base ligands in a square-planar geometry, with a dihedral angle between the two chelate NCuO planes of 31.57 (3)°. The Cu atom is located on a twofold axis.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.105
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: APEX2; software used to prepare material for publication: APEX2.

{4,6-Dichloro-2-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4- yl)iminomethyl]phenolato-κ²N,O}copper(II)

Crystal data

[Cu(C18H14Cl2N3O2)2]	F(000) = 1660
Mr = 813.98	Dx = 1.514 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.4341 (17) Å	Cell parameters from 5244 reflections
b = 6.7434 (5) Å	θ = 2.1–25.0°
c = 22.6048 (16) Å	µ = 0.96 mm^−1
β = 91.570 (1)°	T = 273 K
V = 3570.8 (4) Å^3	Prism, blue
Z = 4	0.34 × 0.16 × 0.13 mm

Data collection

Bruker APEX-II area-detector diffractometer	3172 independent reflections
Radiation source: fine-focus sealed tube	2660 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 25.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→28
Tmin = 0.736, Tmax = 0.885	k = −8→7
10369 measured reflections	l = −26→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0692P)^2 + 0.3862P] where P = (Fo^2 + 2Fc^2)/3
3172 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.0000	0.13084 (6)	0.2500	0.03850 (15)
N1	0.02757 (7)	0.0803 (3)	0.17038 (7)	0.0385 (4)
N2	−0.08406 (8)	−0.1200 (3)	0.07475 (8)	0.0430 (5)
N3	−0.06744 (7)	0.0499 (3)	0.04327 (7)	0.0420 (4)
O1	0.07314 (6)	0.1923 (3)	0.28143 (7)	0.0490 (4)
O2	−0.00544 (8)	0.3147 (3)	0.06217 (8)	0.0569 (5)
C1	−0.01213 (9)	0.0260 (3)	0.12484 (9)	0.0385 (5)
C2	−0.04701 (10)	−0.1319 (3)	0.12329 (10)	0.0421 (5)
C3	−0.02511 (10)	0.1510 (3)	0.07489 (10)	0.0409 (5)
C4	−0.04889 (13)	−0.3040 (4)	0.16436 (12)	0.0627 (7)
H4A	−0.0259	−0.2762	0.1992	0.094*
H4B	−0.0344	−0.4196	0.1451	0.094*
H4C	−0.0876	−0.3274	0.1753	0.094*
C5	−0.09640 (11)	−0.2978 (4)	0.03901 (11)	0.0548 (6)
H5A	−0.0628	−0.3364	0.0186	0.082*
H5B	−0.1265	−0.2693	0.0107	0.082*
H5C	−0.1080	−0.4038	0.0644	0.082*
C6	−0.10449 (10)	0.1333 (3)	−0.00074 (10)	0.0430 (5)
C7	−0.16238 (11)	0.0881 (4)	−0.00231 (11)	0.0565 (7)
H7	−0.1776	0.0069	0.0265	0.068*
C8	−0.19710 (13)	0.1652 (5)	−0.04714 (14)	0.0707 (9)
H8	−0.2356	0.1320	−0.0493	0.085*
C9	−0.17462 (15)	0.2918 (5)	−0.08884 (14)	0.0766 (9)
H9	−0.1979	0.3434	−0.1190	0.092*
C10	−0.11806 (15)	0.3403 (4)	−0.08529 (13)	0.0681 (8)
H10	−0.1035	0.4295	−0.1124	0.082*
C11	−0.08193 (12)	0.2600 (4)	−0.04240 (10)	0.0535 (6)
H11	−0.0432	0.2903	−0.0414	0.064*
C12	0.11991 (9)	0.2175 (3)	0.25324 (9)	0.0393 (5)
C13	0.17017 (9)	0.2768 (3)	0.28486 (10)	0.0404 (5)
C14	0.22127 (9)	0.3076 (3)	0.25816 (11)	0.0452 (6)
H14	0.2533	0.3473	0.2804	0.054*
C15	0.22463 (9)	0.2788 (3)	0.19751 (11)	0.0443 (5)
C16	0.17817 (10)	0.2199 (4)	0.16449 (11)	0.0438 (5)
H16	0.1813	0.2000	0.1240	0.053*
C17	0.12514 (9)	0.1891 (3)	0.19143 (10)	0.0389 (5)
C18	0.07861 (10)	0.1245 (3)	0.15395 (10)	0.0407 (5)
H18	0.0857	0.1131	0.1138	0.049*
Cl1	0.16534 (3)	0.30613 (10)	0.36073 (3)	0.05329 (19)
Cl2	0.28948 (3)	0.31602 (11)	0.16363 (3)	0.0640 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0304 (2)	0.0529 (3)	0.0319 (2)	0.000	−0.00376 (15)	0.000
N1	0.0334 (9)	0.0470 (11)	0.0348 (9)	−0.0017 (8)	−0.0045 (7)	−0.0013 (8)
N2	0.0420 (10)	0.0463 (12)	0.0403 (10)	−0.0063 (8)	−0.0068 (8)	0.0002 (8)
N3	0.0406 (10)	0.0453 (11)	0.0396 (10)	−0.0024 (9)	−0.0082 (8)	0.0007 (8)
O1	0.0348 (8)	0.0762 (12)	0.0359 (9)	−0.0084 (8)	−0.0023 (7)	−0.0031 (7)
O2	0.0655 (12)	0.0514 (11)	0.0531 (11)	−0.0126 (9)	−0.0122 (9)	0.0078 (8)
C1	0.0337 (10)	0.0470 (14)	0.0346 (11)	−0.0003 (10)	−0.0026 (8)	−0.0028 (9)
C2	0.0390 (12)	0.0501 (14)	0.0370 (12)	−0.0027 (10)	−0.0025 (9)	0.0001 (9)
C3	0.0367 (11)	0.0453 (14)	0.0404 (12)	−0.0021 (10)	−0.0035 (9)	−0.0034 (10)
C4	0.0687 (18)	0.0607 (18)	0.0577 (17)	−0.0159 (14)	−0.0152 (13)	0.0118 (13)
C5	0.0568 (15)	0.0538 (16)	0.0531 (15)	−0.0106 (12)	−0.0112 (12)	−0.0024 (12)
C6	0.0446 (13)	0.0494 (15)	0.0344 (12)	0.0070 (10)	−0.0088 (9)	−0.0067 (10)
C7	0.0487 (14)	0.0694 (18)	0.0506 (14)	0.0037 (12)	−0.0119 (11)	−0.0071 (12)
C8	0.0554 (17)	0.086 (2)	0.0689 (19)	0.0164 (15)	−0.0231 (15)	−0.0112 (16)
C9	0.085 (2)	0.078 (2)	0.0644 (19)	0.0188 (18)	−0.0324 (17)	0.0016 (16)
C10	0.092 (2)	0.0595 (18)	0.0516 (16)	0.0049 (15)	−0.0200 (15)	0.0060 (13)
C11	0.0649 (16)	0.0508 (16)	0.0442 (14)	0.0026 (13)	−0.0105 (11)	−0.0042 (11)
C12	0.0361 (11)	0.0409 (13)	0.0407 (12)	−0.0015 (10)	−0.0050 (9)	0.0024 (9)
C13	0.0375 (11)	0.0400 (13)	0.0433 (12)	0.0007 (10)	−0.0077 (9)	−0.0013 (10)
C14	0.0373 (12)	0.0372 (13)	0.0605 (16)	−0.0018 (10)	−0.0107 (11)	−0.0016 (10)
C15	0.0330 (11)	0.0369 (13)	0.0630 (15)	−0.0024 (10)	0.0039 (10)	0.0020 (10)
C16	0.0410 (12)	0.0452 (14)	0.0452 (13)	−0.0009 (11)	0.0017 (10)	−0.0001 (10)
C17	0.0325 (11)	0.0426 (13)	0.0413 (12)	−0.0015 (9)	−0.0021 (9)	−0.0003 (9)
C18	0.0400 (12)	0.0467 (14)	0.0352 (11)	−0.0002 (10)	−0.0015 (9)	−0.0008 (9)
Cl1	0.0507 (4)	0.0640 (4)	0.0444 (4)	0.0004 (3)	−0.0132 (3)	−0.0078 (3)
Cl2	0.0387 (3)	0.0662 (5)	0.0876 (5)	−0.0094 (3)	0.0130 (3)	−0.0052 (3)

Geometric parameters (Å, º)

Cu1—O1^i	1.8835 (15)	C6—C7	1.390 (3)
Cu1—O1	1.8835 (15)	C7—C8	1.384 (4)
Cu1—N1	1.9587 (17)	C7—H7	0.9300
Cu1—N1^i	1.9587 (17)	C8—C9	1.386 (5)
N1—C18	1.297 (3)	C8—H8	0.9300
N1—C1	1.417 (3)	C9—C10	1.366 (5)
N2—C2	1.383 (3)	C9—H9	0.9300
N2—N3	1.409 (3)	C10—C11	1.380 (4)
N2—C5	1.470 (3)	C10—H10	0.9300
N3—C3	1.386 (3)	C11—H11	0.9300
N3—C6	1.419 (3)	C12—C13	1.418 (3)
O1—C12	1.294 (2)	C12—C17	1.419 (3)
O2—C3	1.233 (3)	C13—C14	1.371 (3)
C1—C2	1.342 (3)	C13—Cl1	1.733 (2)
C1—C3	1.435 (3)	C14—C15	1.389 (3)
C2—C4	1.488 (3)	C14—H14	0.9300
C4—H4A	0.9600	C15—C16	1.362 (3)
C4—H4B	0.9600	C15—Cl2	1.739 (2)
C4—H4C	0.9600	C16—C17	1.414 (3)
C5—H5A	0.9600	C16—H16	0.9300
C5—H5B	0.9600	C17—C18	1.430 (3)
C5—H5C	0.9600	C18—H18	0.9300
C6—C11	1.387 (3)
O1^i—Cu1—O1	154.58 (11)	C11—C6—N3	118.9 (2)
O1^i—Cu1—N1	90.65 (7)	C7—C6—N3	120.6 (2)
O1—Cu1—N1	93.73 (7)	C8—C7—C6	119.4 (3)
O1^i—Cu1—N1^i	93.73 (7)	C8—C7—H7	120.3
O1—Cu1—N1^i	90.65 (7)	C6—C7—H7	120.3
N1—Cu1—N1^i	159.96 (11)	C7—C8—C9	120.2 (3)
C18—N1—C1	116.35 (17)	C7—C8—H8	119.9
C18—N1—Cu1	123.59 (15)	C9—C8—H8	119.9
C1—N1—Cu1	119.08 (13)	C10—C9—C8	119.6 (3)
C2—N2—N3	105.76 (17)	C10—C9—H9	120.2
C2—N2—C5	119.9 (2)	C8—C9—H9	120.2
N3—N2—C5	116.01 (18)	C9—C10—C11	121.5 (3)
C3—N3—N2	110.10 (17)	C9—C10—H10	119.2
C3—N3—C6	125.6 (2)	C11—C10—H10	119.2
N2—N3—C6	120.26 (18)	C10—C11—C6	118.7 (3)
C12—O1—Cu1	128.14 (13)	C10—C11—H11	120.6
C2—C1—N1	127.7 (2)	C6—C11—H11	120.6
C2—C1—C3	109.25 (19)	O1—C12—C13	119.5 (2)
N1—C1—C3	122.7 (2)	O1—C12—C17	124.35 (19)
C1—C2—N2	110.07 (19)	C13—C12—C17	116.2 (2)
C1—C2—C4	129.1 (2)	C14—C13—C12	122.9 (2)
N2—C2—C4	120.8 (2)	C14—C13—Cl1	119.99 (17)
O2—C3—N3	126.0 (2)	C12—C13—Cl1	117.07 (17)
O2—C3—C1	129.5 (2)	C13—C14—C15	119.2 (2)
N3—C3—C1	104.47 (19)	C13—C14—H14	120.4
C2—C4—H4A	109.5	C15—C14—H14	120.4
C2—C4—H4B	109.5	C16—C15—C14	121.0 (2)
H4A—C4—H4B	109.5	C16—C15—Cl2	119.72 (19)
C2—C4—H4C	109.5	C14—C15—Cl2	119.24 (17)
H4A—C4—H4C	109.5	C15—C16—C17	120.4 (2)
H4B—C4—H4C	109.5	C15—C16—H16	119.8
N2—C5—H5A	109.5	C17—C16—H16	119.8
N2—C5—H5B	109.5	C16—C17—C12	120.3 (2)
H5A—C5—H5B	109.5	C16—C17—C18	117.0 (2)
N2—C5—H5C	109.5	C12—C17—C18	122.6 (2)
H5A—C5—H5C	109.5	N1—C18—C17	126.5 (2)
H5B—C5—H5C	109.5	N1—C18—H18	116.8
C11—C6—C7	120.5 (2)	C17—C18—H18	116.8

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2	0.93	2.49	2.950 (3)	111
C5—H5A···O2^ii	0.96	2.46	3.352 (3)	154

Symmetry code: (ii) −x, −y, −z.